Synthesis, Characterization, X-ray Structure and Biological Activities of C-5-Bromo-2-hydroxyphenylcalix[4]-2-methyl resorcinarene

Autor: Mamoru Koketsu, Seow Chew Low, Nazlina Ibrahim, Mukram Mohamed Mackeen, Siti Aishah Hasbullah, Hamza M. Abosadiya, Bohari M. Yamin
Jazyk: angličtina
Rok vydání: 2013
Předmět:
Zdroj: Molecules, Vol 18, Iss 11, Pp 13369-13384 (2013)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules181113369
Popis: C-5-bromo-2-hydroxyphenylcalix[4]-2-methylresorcinarene (I) was synthesized by cyclocondensation of 5-bromo-2-hydroxybenzaldehyde and 2-methylresorcinol in the presence of concentrated HCl. Compound I was characterized by infrared and nuclear magnetic resonance spectroscopic data. X-ray analysis showed that this compound crystallized in a triclinic system with space group of Pī, a = 15.9592(16)Å, b = 16.9417(17)Å, c = 17.0974(17)Å, α = 68.656(3)°, β = 85.689(3)°, γ = 81.631(3)°, Z = 2 and V = 4258.6(7)Å3. The molecule adopts a chair (C2h) conformation. The thermal properties and antioxidant activity were also investigated. It was strongly antiviral against HSV-1 and weakly antibacterial against Gram-positive bacteria. Cytotoxicity testing on Vero cells showed that it is non-toxic, with a CC50 of more than 0.4 mg/mL.
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